Last year's biggest cruise was supposed to be 13nm there, eat lunch, 13nm back to the marina, from Sutton's Bay to Northport in Lake Michigan- 26 nautical miles in one day.
no wind
We had plenty of gas, but I really didn't want to motor, so we gave up about half way there. We did manage to find a "sail up" restaurant and had a nice lunch at what was probably the 6 mile marker. It was a great day on the water, but we didn't make our destination.
This year I'm considering Escanaba to Fayette in the Bays de Noc (Lake Michigan). 21nm each way - return trip the next day.
42 miles in two days, with no real place to stop in between. I guess you just make sure you take plenty of gas.
When you are planning a trip, how far do you expect you can go in one day?